


Holding to on Good

by romeoandjulietyouwish



Series: Lis Writes Mighty Nein [5]
Category: Critical Role (Web Series)
Genre: Alternate Universe - Canon Divergence, Angst with a Happy Ending, Caleb Widogast Deserves Nice Things, Caleb Widogast Needs a Hug, Can be read as slash, Emotional Hurt/Comfort, Gen, Hurt/Comfort, Jester Lavorre & Caleb Widogast Friendship, Self-Esteem Issues, Self-Hatred, Self-Loathing Caleb Widogast
Language: English
Status: Completed
Published: 2020-11-21
Updated: 2020-11-21
Packaged: 2021-03-09 20:13:45
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,949
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27661853
Author URL: https://archiveofourown.org/users/romeoandjulietyouwish/pseuds/romeoandjulietyouwish
Summary: Caleb reading Der Katzen Prinz to Jester sparks up an uncomfortable conversation about happiness.
Relationships: Jester Lavorre & Caleb Widogast
Series: Lis Writes Mighty Nein [5]
Series URL: https://archiveofourown.org/series/2026874
Comments: 12
Kudos: 81





	Holding to on Good

**Author's Note:**

> You guys...I love them so much (I haven't seen 116 yet so please no spoilers)

As he retires to his room for the night, Caleb hangs up his coat, checking and rechecking that all of his components are in the proper place. He toes off his boots, soaking wet from the snow, and sets them neatly by the door. Caleb moves to sit at his desk to study for a bit when a knock comes at the door.

He walks briskly over to it and when he opens it he smiles, actually smiles. On the other side is Jester, dressed in soft pajamas and her hair is wound into two braids that she must have convinced Veth to do for her. 

“Could you cast Tongues on me?” She asks immediately. 

Instead of just doing the simple spell, Caleb finds himself offering to read it to her instead. He fully expects her to say no, why wouldn’t she? But Jester just smiles, and waltzes into his room, plopping down on the couch, looking at him expectantly. He quickly dismisses her comments about his nearly bare room and grabs his copy of Der Katzen Prinz off the table.

As Caleb reads, he notices that Jester inches closer and closer to him, leaning over his shoulder to look at the pictures. He holds it out a little more for her, but it doesn’t seem to make a difference. As he turns the third to the last page, her head falls onto his shoulder. He stiffens for an instant, but he doesn’t want her to think that her touch is unwelcome so he forces himself to relax. He tries his best to focus on reading and translating as opposed to the tiefling curled up next to him, her hair falling onto his collarbone and her side pressed against his. 

When he reads the final line and closes the book, Jester lifts her head from his shoulder, yawning with a stretch. He gets up to put the book away, he tries to hide how quickly he stands, but he knows she must see how quickly he darts away from her. 

Caleb wishes he could explain that it has absolutely nothing to do with her and everything to do with him and his own weakness. Caleb takes his time slotting the book back into its place, feeling Jester’s eyes on him the whole time. 

When he turns back to her, her chin is resting on her knees and she’s looking at him with curiosity. “Does that book make you happy, Caleb?” She asks. 

He nods, not quite sure where she’s going with this. “Ja, ja it does.” 

“Does spending time with me make you happy?” She blinks her big eyes at him. 

Caleb laughs a little to hide his discomfort. “It does.”

She hums and looks him over, her eyes seeming to peer straight through him. “Why do you look sad then?” He doesn’t answer, choosing instead to look at his shoes. “Caleb, why don’t you like being happy?” 

“I-I’m not sure what you mean,” Caleb lies. 

“Yes, you do.” Jester rises from the couch and walks to him, her arms crossed. “Every time you’re even a little bit happy, you get really sad. Why don’t you like it?” 

Caleb sighs, wrapping his arms around himself, “Jester...it’s very complicated. I am not a good person-”

“You’re not a bad person, Caleb,” Jester glares at him as if daring him to say another bad word about himself. “Bad things happened to you. There’s a difference.” 

“I’m a murderer,” Caleb takes a step away from her as his voice rises in volume. “I killed my mother and father in cold blood. I have done awful things to people who didn’t deserve it.” He takes a long breath, he doesn’t mean to yell at her. “I don’t deserve to be happy.” 

“Caleb…” Jester’s eyes rapidly fill with tears. And Caleb hates himself even more. He made her upset. They were having a nice time together and now he made her cry. He should have kept his distance like he told himself he should. He should have just cast Tongues on her when she asked. Jester opens her mouth a few times, but it seems she comes up with nothing to say. 

Caleb sighs, “I’m sorry, Jester.” 

He doesn’t say anything more to her, he just walks into his bedroom, closing the door behind him. He waits a few moments before hearing the main door to his chambers close. With Jester gone, Caleb sinks down against the wall, burying his head in his hands, his legs tucked up to his chest. His arms ache.

* * *

  
When Jester wakes up in the morning, she feels heavy. It took her forever to fall asleep last night, she couldn’t get her conversation with Caleb out of her mind. It hurts her to know how bad he’s hurting. She knew that he’s been through terrible things, but what strikes Jester is that she never realized how much Caleb struggles inside his own mind. 

How can he believe that he doesn’t deserve happiness? 

Jester takes her time getting ready, still mulling over the conversation. 

He had been so kind to her when he had read her that book. He had let her put her head on his shoulder and he started doing voices for the characters. But as soon as the book had closed, he was suddenly so cruel to himself. He seemed so happy just seconds before. 

Scratching on the door draws Jester’s attention. She opens it up to see Frumpkin on the other side. He looks up at her and then meows loudly, winding between her legs. “Good morning,” Jester smiles at the cat, reaching down to scratch his head. Frumpkin rubs against her legs and then begins to walk away from her. After a second he turns around and meows at Jester again. 

She smiles, “You want me to follow you?” The cat meows again and Jester takes the hint. No one else seems to be up yet, so Jester takes care to be quiet as she begins to follow the little orange cat. He leads her up through the floors, passing Caleb and Veth’s rooms and going up, past where she has been so far. 

Frumpkin meows what she assumes would be a few words and they float up again, the brass ceiling opening above them. “Where are we going?” Jester asks him. 

The floor closes beneath them and Jester finds herself in a small room with nine doors. Frumpkin leads her to the sixth one, meowing again at her. Jester gives the cat a curious look but opens the door tentatively. 

Jester’s heart stops when she sees the room. Three wooden chairs with leather straps on the arms and legs sit in the middle of the room, a rolling tray of silver metal tools rests off to the side. The room instills an immediate rush of fear in her and even though it’s not cold she pulls her cape tighter around herself. 

In the corner of the room, she sees Caleb curled in a ball upright against the wall, his coat tucked tightly around himself, fast asleep. And even though he’s sleeping, every muscle in his body is tense. Frumpkin pushes past Jester and runs to her master, pawing gently at his leg. Caleb doesn’t stir so Frumpkin turns to Jester and meows loudly. The sound manages to break her out of her stupor and she dashes across the room to him.

“Caleb?” She asks as she kneels beside him. “It’s time to wake up. Come on.” She gently shakes his shoulder, not wanting to startle him. It takes a few seconds, but Caleb’s eyes blink slowly open.

The second Caleb sees her, scrambles away with his eyes wide, “You’re not supposed to be here. How did you get here?” He demands harshly. 

“Frumpkin brought me. I think he was worried about you.” Caleb looks at his cat with contempt, but Frumpkin just nuzzles against his leg. She sits down on the ground cross-legged. Jester looks around the room, “What is this place, Caleb?”

He shakes a hand through his hair and sighs. “It’s nothing you need to worry about.”

Jester is quiet for a moment as she stares at the three chairs in the middle and the dusty metal tools. Oh. 

She turns to look at the wizard sadly. “It’s where he used to hurt you. Where he put the crystals in your arms.” Caleb doesn’t answer, but his silence tells her all she needs to know. “Why is this place here?”

He tips his head back against the wall. “It’s complicated, Jester. I don’t want to burden you with the-the shit that goes on up here.” He points to his head. 

“Tell me,” she encourages softly. “I won’t judge you, I promise.” 

He looks at her sideways and when she doesn’t break eye contact he sights. “I have a perfect memory,” Caleb begins, looking straight out. “I remember every second of everything that happened to me and every awful and fucked up thing I did. I remember the face of every person hurt and I remember everything about them. But-But when I’m with you all, sometimes I forget for a while. I let myself be caught up in the happiness that I feel when I’m around you all that I don’t think about it.” Jester frowns that sounds like a good thing to her, but she knows that in Caleb’s mind it probably isn’t. 

“This place...it helps me remember. Because I don’t deserve to forget or move on.”

“Caleb…” She shakes her head, scooching closer so their sides are almost pressed together. “You deserve to be happy. You don’t deserve to torture yourself with horrible memories.” She takes his hand and Caleb inhales as if the touch is painful to him. But he doesn’t let go. “We’ve all done bad things, we’ve all hurt people.”

“It’s not-”

“I know it’s not exactly the same thing,” she squeezes his hand, “and none of us can ever really understand what you went through, but we can be here for you. I can be here for you. I’m your friend, Caleb. I want to help you.” 

“I don’t deserve-”

“Will you shut up about what you deserve?” Jester moves so that she is sitting right in front of him. He looks at her a little nervously. She looks him right in the eyes as she tells him, “You deserve to be happy. You deserve friends that love you. You deserve to be safe and taken care of. And,” she opens her arms to him, “you deserve the hug I am about to give you.” 

She leans forward, pulling Caleb into her arms. Just like when she put her head on his shoulder last night, Caleb immediately stiffens. But she doesn’t let go and after a moment or so, Caleb sags in her arms. She just holds him and eventually, she feels him start to sob against her shoulder. His arms are tight around her waist and Jester squeezes him just the same amount. 

“I’m sorry,” he whispers into her shoulder. 

“That’s stupid, you have nothing to be sorry for,” she tells him. 

She doesn’t know how long they hug, but eventually, her legs begin to ache and Caleb draws away from her. He drags a hand down his face, wiping away the last of his tears. “Thank you, Jester.” 

She smiles at him, “Of course, silly, that’s what friends are for.” She extends her hand to him and he takes it easily. 

Jester keeps her hand in his as she leads him out of the dim room and back down into the tower where all of their friends are just starting to wake up. 

**Author's Note:**

> Comments and kudos are always appreciated! Thank you so much for reading!
> 
> Tumblr- @romeoandjulietyouwish


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